Holiday Homes in Kailua

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Featured Holiday Homes in Kailua

Viewhouse in Lanikai BEST LOCATION , LANIKAI NUC 90/BB -0108

9.6 out of 10, Exceptional, (64)
"Perfect location for a great beach trip"
Viewhouse in Lanikai BEST LOCATION , LANIKAI NUC 90/BB -0108

Hale Aloha - AC, Beachfront

Hale Aloha - AC, Beachfront

Aloha Adventure Home - 2 min from beach

9.2 out of 10, Wonderful, (21)
"Good location, n"
Aloha Adventure Home - 2 min from beach

Ocean Front Center of Kailua Bay! Best Location!!

10.0 out of 10, Exceptional, (27)
"Best place for families, our whole family enjoyed our time together in this great place!"
Ocean Front Center of Kailua Bay! Best Location!!

Sunset View Oasis - Steps from beach

6.0 out of 10, (3)
"Great convenient location and plenty of room for our family"
Sunset View Oasis - Steps from beach

Oceanside Estate - Spacious home with Pool & AC

9.6 out of 10, Exceptional, (4)
"Was a great stay"
Oceanside Estate - Spacious home with Pool & AC

Oahu Paradise - AC, 1 block to beach!

8.2 out of 10, Very good, (11)
"We really enjoyed our stay here, the location is perfect and the home was clean, comfortable, and had lots of room for our large group of 8. The only reason we couldn’t give a perfect score was a few maintenance issues, like running toilets, one room with an unusable fan, and the kitchen sink sprayer that would jam on. All minor issues, we would definitely stay here again! "
Oahu Paradise - AC, 1 block to beach!

Experience the Beauty of Paradise, Stunning Gardens, Steps from Kailua Beach

9.6 out of 10, Exceptional, (187)
"Parking tight, mobility tough for handicapped, second bathroom outside, downstairs. Unit could use some TLC. Nice, comfortable furniture & beds. TV on Roku, remote gave us problems, freezer didn’t make ice cubes."
Experience the Beauty of Paradise, Stunning Gardens, Steps from Kailua Beach

Beachfront Private, N. Shore & Legal Vacation!

Beachfront Private, N. Shore & Legal Vacation!

Nani Iki - Close to beach!

10.0 out of 10, Exceptional, (1)
"We had a wonderful time at the Hauula Hideaway. The property is spacious and immaculate. Very clean, comfortable, plenty of space, lots of amenities and excellent communication. We had a plumbing issue when we arrived, but the host and the local contact worked hard and made things right. I'd definitely stay here again!"
Nani Iki - Close to beach!

Kailua Beachside, 2 Houses off beach, 2bed/2bath, Sleeps 8, Ocean & Mtn Views

8.8 out of 10, Excellent, (54)
"Pros: The location is perfect, I counted 200 steps to the beach. The owner provided beach towels, chairs, toys, boogie boards. We love the beach and really enjoyed being able to see the sunrise, go back to sleep, and then having a whole beach day within steps. The shower/bathroom situation was good. We especially loved the outdoor shower and the shower on the lower level being separate from the bathroom. Since everyone fights over who gets to shower first after the beach. They have lots of...
Kailua Beachside, 2 Houses off beach, 2bed/2bath, Sleeps 8, Ocean & Mtn Views

Manoa Valley A 2BR with ocean and mountain views

9.8 out of 10, Exceptional, (46)
"Visited with a group of 4 adults and we each had our own space which was lovely. House is very conveniently located to easily access everywhere we wanted to visit on the island. The house is charming and has a stunning view of the Waikiki shore. Would absolutely stay here again for a future visit!"
Manoa Valley A 2BR with ocean and mountain views

Hawaii Palm B - Beachfront, Hot Tub

8.8 out of 10, Excellent, (16)
"We loved the location and views. We had a 4 bedroom house on the semi private beach. We enjoyed the chickens and the rooster that woke us up so we didn’t miss the beautiful sunrise. We did encounter a few problems first the dryer was broken but texting the caretaker he gave us a code to anther room with a dryer. Our biggest problem was the construction at the other house on the property. We had workers in our parking spaces which we had to ask them to move multiple times. They also turned off...
Hawaii Palm B - Beachfront, Hot Tub

BEACH FRONT KAILUA ESTATE, OCEAN VIEWS, HUGE LUSH PRIVATE HISTORIC PROPERTY

9.0 out of 10, Wonderful, (124)
"Host was excellent with responses and clearly conveying expectations. Property was very pretty and along the beach access our daughter normally uses to get to the beach. Kitchen well accessorized with cooking needs, spices, etc. Our space was shared by family of 2 older adults and 2 younger adults. Stayed for a week of enjoyment, both before and after the wedding. "
BEACH FRONT KAILUA ESTATE, OCEAN VIEWS, HUGE LUSH PRIVATE HISTORIC PROPERTY

Oceanfront Romantic Couple's Getaway with Private Beach w/ Full Living Amenities

9.4 out of 10, Exceptional, (79)
"We loved the place and location. The owners were very nice and helpful to quickly resolve the few issues we had. We loved our stay at the North Shore after spending a few days in Waikiki"
Oceanfront Romantic Couple's Getaway with Private Beach w/ Full Living Amenities

Moani Kai - Beachfront,Gated,Hot tub,Pickleball Ct

9.0 out of 10, Wonderful, (59)
"The location, the company & the island. We loved every minute. Carol, the host, was one of the most thoughtful hosts we have ever come across. We traveled with our 4 teenage kids & my elderly parents and in-laws and Carol helped us get a few extra items we needed to help them feel comfortable. Would highly recommend staying here again. "
Moani Kai - Beachfront,Gated,Hot tub,Pickleball Ct

White Hibiscus B -home on Laie Point, Beach access

10.0 out of 10, Exceptional, (1)
"We traveled as a group of 15, four families, for ten days in Laie point. The house was so great, room for kids to play, adults played cards, and room for large group meals. Each bedroom had a bathroom with shower for each family to retreat to during the day. The view is unbelievable and the semiprivate beach was so special. No one wanted to leave as it was such a special experience."
White Hibiscus B -home on Laie Point, Beach access

Amazing beach house with gorgeous views of the sunrise!

10.0 out of 10, Exceptional, (20)
"Best location on the island with ease of access to all the great small island towns and beaches without all the large city problems. Wonderful small town courtesy, charm, and hospitality, coupled with a wonderful location right across the street from the beach. Disconnect and unwind, Punalu'u is exactly what you and your family need to reconnect to each other in paradise."
Amazing beach house with gorgeous views of the sunrise!

Ocean Getaway -Near Beach w/ AC, Kayak, BBQ and more!

10.0 out of 10, Exceptional, (2)
"The home was absolutely lovely. The hosts were in communication from the beginning. They were available for anything we needed. We adored the wrap around lanai and all the little touches the owners left for us. The home was very kid and adult friendly with a lovely neighborhood and neighbors. I recommend this place for anyone who wants a quiet retreat."
Ocean Getaway -Near Beach w/ AC, Kayak, BBQ and more!

Oceanview Oasis - Ocean views, AC

8.8 out of 10, Excellent, (5)
"This was a great place! We loved staying there and spending each morning out on the rock pool, watching the ocean. One morning we had two sea turtles! The place was clean, the local coordinator was kind and we made lasting memories at the Pineapple Paradise!"
Oceanview Oasis - Ocean views, AC
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Kailua

BEACH FRONT KAILUA ESTATE, OCEAN VIEWS, HUGE LUSH PRIVATE HISTORIC PROPERTY

9.0 out of 10, Wonderful, (124)
"Host was excellent with responses and clearly conveying expectations. Property was very pretty and along the beach access our daughter normally uses to get to the beach. Kitchen well accessorized with cooking needs, spices, etc. Our space was shared by family of 2 older adults and 2 younger adults. Stayed for a week of enjoyment, both before and after the wedding. "
BEACH FRONT KAILUA ESTATE, OCEAN VIEWS, HUGE LUSH PRIVATE HISTORIC PROPERTY

Private Beachfront Rental

9.8 out of 10, Exceptional, (214)
"This location gave us the perfect beachfront oasis we were looking for! The accommodations were clean and well kept. The bed was comfortable with soft sheets and perfectly fluffed pillows. Shari made check in and out a breeze. She also gave us a lot of local restaurant recommendations which were worth absolutely worth the hype! If you are looking for a private and peaceful beachfront getaway, I highly recommend this spot! "
Private Beachfront Rental

Aston Waikiki Sunset

4.0 star property
7.8 out of 10, Good, (2840)
"Our stay at Aston Waikīkī Sunset exceeded our expectations. It’s not a luxury 5 star hotel but we needed accommodations for 6 within a month. We booked a 2 bedroom suite with a queen bed in one room, 2 twin beds in the other bedroom and a queen sofa sleeper in the living area. It was perfect for us and was walking distance to the beach, dining and shopping. We would definitely stay here again! Mahalo!"
The price is AU$405
includes taxes & fees
23 Dec - 24 Dec
Aston Waikiki Sunset
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.